tert-butyl N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate

Base Information

• Chemical Name: tert-butyl N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
• CAS No.: 33900-15-1
• Molecular Formula: C20H31N3O4
• Molecular Weight: 377.484
• DSSTox Substance ID: DTXSID90428572
• Wikidata: Q82241403
• Mol file: 33900-15-1.mol

Synonyms:33900-15-1;tert-butyl N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate;AC1OKG3K;Boc-Leu-Phe-NH2;DTXSID90428572;AKOS027447793

Chemical Property of tert-butyl N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate

Chemical Property:

• Melting Point: 83-85 °C
• Boiling Point: 615.6±55.0 °C(Predicted)
• PSA: 118.49000
• Density: 1.108±0.06 g/cm3(Predicted)
• LogP: 4.33300
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 377.23145648
• Heavy Atom Count: 27
• Complexity: 508

Purity/Quality:

N-[(1,1-Dimethylethoxy)carbonyl]-L-leucyl-L-phenylalaninamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)NC(CC1=CC=CC=C1)C(=O)N)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N)NC(=O)OC(C)(C)C
• Uses: N-[(1,1-Dimethylethoxy)carbonyl]-L-leucyl-L-phenylalaninamide is an intermediate in the synthesis of γ-Secretase Inhibitor, the enzyme complex that catalyzes the cleavage of the amyloid precursor protein (APP) to generate amyloid β-peptide (Aβ), the major causative agent in Alzheimer disease (AD).

Technology Process of tert-butyl N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate

There total 8 articles about tert-butyl N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + L-Phenylalanine amide (5241-58-7) → (2S)-N-[(1S)-2-amino-1-benzyl-2-oxoethyl]-2-[(tert-butoxycarbonyl)amino]-4-methylpentanamide (33900-15-1)

Guidance literature:

N-tert-butoxycarbonyl-L-leucine; With sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

L-Phenylalanine amide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 20h;

DOI:10.1055/s-2003-37649

Reference yield: 46.0%

L-Phenylalanine amide (5241-58-7) + N-tert-butoxycarbonyl-L-leucine methyl ester (63096-02-6) → (2S)-N-[(1S)-2-amino-1-benzyl-2-oxoethyl]-2-[(tert-butoxycarbonyl)amino]-4-methylpentanamide (33900-15-1)

Guidance literature:

With subtilisin 8350; triethylamine; In water; N,N-dimethyl-formamide; for 0.583333h; pH 8.5-9.0;

DOI:10.1021/ja00159a006

Reference yield:

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) → (2S)-N-[(1S)-2-amino-1-benzyl-2-oxoethyl]-2-[(tert-butoxycarbonyl)amino]-4-methylpentanamide (33900-15-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-hydroxybenzotriazole (HOBT), 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDC) / dimethylformamide / 18 h / Ambient temperature

2: triethylamine / 1,2-dimethoxy-ethane / 18 h / Ambient temperature

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00113a025

upstream raw materials:

L-Phenylalanine amide

(S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoic acid pyridin-2-yl ester

Boc-Leu-ONSu

(S)-2-amino-3-phenylpropionamide hydrochloride

Downstream raw materials:

{(1S)-benzyl-(4R)-[1-((1S)-carbamoyl-2-phenyl-ethylcarbamoyl)-(1S)-3-methyl-butyl-carbamoyl]-(2S)-hydroxy-5-phenyl-pentyl} carbamic acid tert-butyl ester

{(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester

(5S)-(tert-butoxycarbonylamino)-6-phenyl-(4R)-hydroxy-(2R)-benzylhexanoyl-L-leucy-L-phenylalaninamide

{(1S,2R,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester

Refernces

• 1、 Dias, Luiz C.,Ferreira, Andrea A.,Diaz, Gaspar. "Short total synthesis of aspartyl protease inhibitors L-685,434, L-682,679 and L-685,458". . p. 1845 - 1849. Retrieved 2007/10/03.
• 2、 Wong,Chen,Hennen,Bibbs,Wang,L iu,Pantoliano,Whitlow,Bryan. "Enzymes in organic synthesis: Use of subtilisin and a highly stable mutant derived from multiple site-specific mutations". . p. 945 - 953. Retrieved 2007/10/02.